Advertisement

Nitrosoureas

  • J. A. Montgomery
  • T. P. Johnston

Abstract

The nitrosoureas were the first class of compounds derived from a lead compound identified by the random screening program of the National Cancer Institute to show useful activity against human cancer1. The activity of N-methyl-N-nitrosourea (1), not only against L 1210’leukaemia implanted intraperitoneally in the usual manner, but against the intracerebrally implanted disease, which contrasted with the inactivity of standard clinical agents such as methotrexate, 6-mercaptopurine, 5-fluorouracil, and cyclophosphamide2, led to a drug development programme that resulted in the identification of the 2-chloro- and 2-fluoroethylnitrosoureas (2) as agents with a high level of activity against a variety of murine neoplasms followed by the establishment of the clinical activity of the 2-chloroethyl compounds3–5.

Keywords

Ergot Alkaloid Nitroso Compound Nitroso Group Amino Acid Amide ANTITUMOUR Agent 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    S. A. Schepartz, Cancer Treat. Rep. 60 (1976) 647.Google Scholar
  2. 2.
    H. E. Skipper, F. M. Schabel, Jr, M. W. Trader and J. R. Thomson, Cancer Res. 21 (1961) 1154.Google Scholar
  3. 3.
    J. A. Montgomery, Cancer Treat. Rep. 60 (1976) 651.Google Scholar
  4. 4.
    J. A. Montgomery, in Chronicles of Drug Discovery, Vol. 2, eds. J. Bindra and D. Lednicer, John Wiley, New York (1983) p. 189.Google Scholar
  5. 5.
    T. P. Johnston and J. A. Montgomery, Cancer Treat. Rep. 70 (1986) 13.Google Scholar
  6. 6.
    T. H. Wasserman, M. Slavik and S. K. Carter, Cancer 36 (1975) 1258.CrossRefGoogle Scholar
  7. 7.
    F. M. Schabel, Jr., T. P. Johnston, G. S. McCaleb, J. A. Montgomery, W. R. Laster and H. E. Skipper, Cancer Res. 23 (1963) 725.Google Scholar
  8. 8.
    O. S. Selawry and H. H. Hansen, Proc. Am. Assoc. Cancer Res. 13 (1972) 46.Google Scholar
  9. 9.
    T. Anderson, V. T. DeVita and R. C. Young. Cancer Treat. Rep. 60 (1976) 761.Google Scholar
  10. 10.
    J. S. Kovach, C. G. Moertel, A. J. Schutt, R. G. Hahn and R. J. Reitemier, Cancer 33 (1974) 563.CrossRefGoogle Scholar
  11. 11.
    H. O. Douglass, Jr., P. T. Lavin and C. G. Moertel, Cancer Treat. Rep. 60 (1976) 769.Google Scholar
  12. 12.
    C. G. Moertel, A. J. Schutt, R. G. Hahn and R. J. Reitemeier. J. Natl. Cancer Inst. 54 (1975) 69.Google Scholar
  13. 13.
    B. Fisher, N. Wolmark, H. Rockette, C. Redmond, M. Deutsch D. L. Wickerham, E. R. Fisher, R. Caplan, J. Jones, H. Lerner, P. Gordon, M. Feldman, A. Cruz, S. LeGault-Poisson, M. Wexler, W. Lawrence, A. Robidoux and other NSABP Investigators, J. Natl. Cancer Inst. 80 (1988) 21.CrossRefGoogle Scholar
  14. 14.
    N. Wolmark, B. Fisher, H. Rockette, C. Redmond, D. L. Wickerham, E. R. Fisher, J. Jones, A. Glass, H. Lerner, W. Lawrence, D. Prager, M. Wexler, J. Evans, A. Cruz, N. Dimitrov, P. Jochimsen and other NSABP Investigators, J. Natl. Cancer Inst. 80 (1988) 30.CrossRefGoogle Scholar
  15. 15.
    P. S. Schein, M. J. O’Connell, J. Blom, S. Hubbard, I. T. Magrath, P. A. Bergevin, P. H. Wiernik, J. L. Ziegler and V. T. DeVita, Cancer 34 (1974) 993.CrossRefGoogle Scholar
  16. 16.
    P. Schein, R. Kahn, P. Gorden, S. Wells and V. T. DeVita, Arch. Intern. Med. 132 (1973) 555.CrossRefGoogle Scholar
  17. 17.
    C. R. Kahn, A. G. Levy, J. D. Gardner, J. V. Miller, P. Gorden and P. S. Schein. N. Engl. J. Med. 292 (1975) 941.CrossRefGoogle Scholar
  18. 18.
    L. E. Broder and S. K. Carter, Ann. Intern. Med. 19 (1973) 108.Google Scholar
  19. 19.
    C. Hansch, A. Leo, C. Schmidt, P. Y. C. Jow and J. A. Montgomery, J. Med. Chem. 23 (1980) 1095.CrossRefGoogle Scholar
  20. 20.
    J. A. Montgomery, G. S. McCaleb, T. P. Johnston, J. G. Mayo and W. R. Laster, Jr., J. Med. Chem. 20 (1977) 291.CrossRefGoogle Scholar
  21. 21.
    F. A. Schmid, G. M. Otter, G. C. Perri, D. J. Hutchison and F. S. Philips. Cancer Res. 43 (1983) 976.Google Scholar
  22. 22.
    T. P. Johnston, G. S. McCaleb and J. A. Montgomery. J. Med. Chem. 6 (1963) 669.CrossRefGoogle Scholar
  23. 23.
    A.W. Prestayko, L.H. Baker, S.T. Crooke, S.K. Carter and P.S. Schein, eds, in Nitrosoureas: Current Status and New Developments, Academic Press, New York (1981).Google Scholar
  24. 24.
    T. Anderson, M.G. McMenamin and P. S. Schein, Cancer Res. 35 (1975) 761.Google Scholar
  25. 25.
    P. S. Schein, M. G. McMenamin and T. Anderson, Cancer Res. 33 (1973) 2005.Google Scholar
  26. 26.
    M. Aoshima and Y. Sakurai, Gann 68 (1977) 247.Google Scholar
  27. 27.
    L. C. Panasci, P. A. Fox and P. S. Schein, Cancer Res. 37 (1977) 3321.Google Scholar
  28. 28.
    P. A. Fox, L. C. Panasci and P. S. Schein, Cancer Res. 37 (1977) 783.Google Scholar
  29. 29.
    T. P. Johnston, G. S. McCaleb and J. A. Montgomery, J. Med. Chem. 18 (1975) 104.CrossRefGoogle Scholar
  30. 30.
    D. Green, K. D. Tew, T. Hisamatsu and P. S. Schein, Biochem. Pharmacol. 31 (1982) 1671.CrossRefGoogle Scholar
  31. 31.
    L. C. Panasci, D. Green and P. S. Schein, J. Clin. Invest. 64 (1979) 1103.CrossRefGoogle Scholar
  32. 32.
    J. D. Ahlgren, D. C. Green, K. D. Tew and P. S. Schein, Cancer Res. 42 (1982) 2605.Google Scholar
  33. 33.
    A. Horikoshi, R. Smith, and M. J. Murphy, Jr, Chemotherapy 29 (1983) 135.CrossRefGoogle Scholar
  34. 34.
    H. E. Kann, Jr, M. A. Schott and A. Petkas, Cancer Res. 40 (1980) 50.Google Scholar
  35. 35.
    H. E. Kann, Jr, B. A. Blumenstein, A. Petkas and M. A. Schott, Cancer Res. 40 (1980) 771.Google Scholar
  36. 36.
    L. H. Schmidt, Unpublished report to the National Cancer Institute, 1972.Google Scholar
  37. 37.
    R. A. Kramer and M. R. Boyd, J. Pharm. Exp. Ther. 227 (1983) 409.Google Scholar
  38. 38.
    R. A. Kramer and M. R. Boyd Proc. Am. Assoc. Cancer Res. 25 (1984) 380.Google Scholar
  39. 39.
    K. W. Kohn, Cancer Res. 37 (1977) 1450.Google Scholar
  40. 40.
    R. A. G. Ewig and K. W. Kohn, Cancer Res. 37 (1977) 2114.Google Scholar
  41. 41.
    R. K. Johnson, L. F. Faucette, I. Wodinsky and J. J. Clement Proc. Am. Assoc. Cancer Res. 23 (1982) 166.Google Scholar
  42. 42.
    J.A. Montgomery, Prog. Cancer Res. Ther. 28 (1983) 1.Google Scholar
  43. 43.
    K.A. Hyde, E. Acton, W.A. Skinner, L. Goodman, J. Greenberg and B.R. Baker, J. Med Pharm. Chem. 5 (1962) 1.CrossRefGoogle Scholar
  44. 44.
    J.A. Montgomery, R. James, G.S. McCaleb and T.P. Johnston, J. Med. Chem. 10 (1967)Google Scholar
  45. 45.
    J.A. Montgomery, R. James, G.S. McCaleb, M.C. Kirk and T.P. Johnston, J. Med. Chem. 18 (1975) 568.CrossRefGoogle Scholar
  46. 46.
    M. Colvin, R.B. Brundrett, W. Cowens, I. Jardine and D.B. Ludlum, Biochem. Pharmacol. 25 (1976) 695.CrossRefGoogle Scholar
  47. 47.
    G.P. Wheeler and S. Chumley, J. Med. Chem. 10 (1967) 259.CrossRefGoogle Scholar
  48. 48.
    G.P. Wheeler. B.J. Bowdon, J.A. Grimsley and H.H. Lloyd, Cancer Res. 34 (1974) 194.Google Scholar
  49. 49.
    Y.F. Shealy, C.A. Krauth and W.R. Laster, Jr., J. Med. Chem. 21 (1984) 664.CrossRefGoogle Scholar
  50. 50.
    J.K. Snyder and L.M. Stock, J. Org. Chem. 45 (1980) 1990.CrossRefGoogle Scholar
  51. 51.
    J.W. Lown and S.M.S. Chauhan, J. Org. Chem. 46 (1981) 5309.CrossRefGoogle Scholar
  52. 52.
    N. Buckley, J. Org. Chem. 52 (1987) 484.CrossRefGoogle Scholar
  53. 53.
    W.P. Tong, K.W. Kohn and D.B. Ludlum, Cancer Res. 42 (1982) 4460.Google Scholar
  54. 54.
    S. Parker, M.C. Kirk, D.B. Ludlum, R.R. Koganty and J.W. Lown, Biochem. Biophys. Res. Commun. 139 (1986) 31.CrossRefGoogle Scholar
  55. 55.
    W.P. Tong, M.C. Kirk and D.B. Ludlum, Cancer Res. 42 (1982) 3102.Google Scholar
  56. 56.
    R.W. Balsiger, A.L. Fikes, T.P. Johnston and J.A. Montgomery, J. Org. Chem. 26 (1961) 3446.CrossRefGoogle Scholar
  57. 57.
    J.R. Piper, A.G. Laseter, T.P. Johnston and J.A. Montgomery, J. Med. Chem. 23 (1980) 1136.CrossRefGoogle Scholar
  58. 58.
    D.B. Ludlum, J.R. Mehta and W.P Tong, Cancer Res. 46 (1986) 3353.Google Scholar
  59. 59.
    W.J. Bodell, K. Tokuda and D.B. Ludlum, Cancer Res. 48 (1988) 4489.Google Scholar
  60. 60.
    D. B. Yarosh, S. Hurst-Calderone, M. A. Babich and R. S. Day III, Cancer Res. 46 (1986) 1663.Google Scholar
  61. 61.
    M. E. Dolan, G. S. Young and A. E. Pegg, Cancer Res. 46 (1986) 4500.Google Scholar
  62. 62.
    G. P. Wheeler, Unpublished data.Google Scholar
  63. 63.
    K. D. Tew and P. S. Schein, Handb. Exp. Pharmakol. 12 (1984) 425.Google Scholar
  64. 64.
    H. E. Skipper, F. M. Schabel, Jr., L. B. Mellett, J. A. Montgomery, L. J. Wilkoff, H. H. Loyd and R. W. Brockman, Cancer Chemother. Rep. 54 (1970) 431.Google Scholar
  65. 65.
    N. J. Harper, J. Med. Pharm. Chem. 1 (1959) 467.CrossRefGoogle Scholar
  66. 66.
    T. P. Johnston, G. S. McCaleb, P. S. Opliger and J. A. Montgomery, J. Med. Chem. 9 (1966) 892.CrossRefGoogle Scholar
  67. 67.
    T. P. Johnston, G. S. McCaleb, W. C. Rose and J. A. Montgomery, J. Med. Chem. 21 (1984) 97.CrossRefGoogle Scholar
  68. 68.
    W. Cowens, R. Brundrett and M. Colvin, Proc. Am. Assoc. Cancer Res., ASCO 16 (1975) 100.Google Scholar
  69. 69.
    R. B. Brundrett, J. W. Cowens and M. Colvin, Proc. Am. Assoc. Cancer Res., ASCO 17 (1976) 102.Google Scholar
  70. 70.
    M. Berger, W. J. Zeller, G. Eisenbrand, P. Z. Lin, M. Nakra and D. Schmahl, Arzneim.- Forsch./Drug Res. 32 (1982) 481.Google Scholar
  71. 71.
    T. Suami, T. Kato, H. Takino and T. Hisamatsu, J. Med. Chem. 25 (1982) 829.CrossRefGoogle Scholar
  72. 72.
    M. Rodriguez, J.-L. Imbach and J. Martinez, J. Med. Chem. 21 (1984) 1222.CrossRefGoogle Scholar
  73. 73.
    R. B. Brundrett, M. Colvin, E. H. White, J. McKee, P. E. Hartmann and D. L. Brown, Cancer Res. 39 (1979) 1328.Google Scholar
  74. 74.
    K. Tsujihara, M. Ozeki, T. Morikawa and Y. Arai, Chem. Pharm. Bull. 29 (1981) 2509.Google Scholar
  75. 75.
    K. Tsujihara, M. Ozeki, T. Morikawa, N. Taga, M. Miyazaki, M. Kawamori and Y. Arai. Chem. Pharm. Bull. 29 (1981) 3262.Google Scholar
  76. 76.
    T. Morikawa, M. Ozeki, N. Umino, M. Kawamori, Y. Arai and K. Tsujihara, Chem. Pharm. Bull. 30 (1982) 534.Google Scholar
  77. 77.
    T. Morikawa, M. Takeda, Y. Arai and K. Tsujihara, Chem Pharm. Bull. 30 (1982) 2386.Google Scholar
  78. 78.
    T. Morikawa, K. Tsujihara, M. Takeda and Y. Arai, Chem. Pharm. Bull. 30 (1982) 4365.Google Scholar
  79. 79.
    T. Morikawa, K. Tsujihara, M. Takeda and Y. Arai, Chem. Pharm. Bull. 31 (1983) 3924.Google Scholar
  80. 80.
    T. Morikawa, K. Tsujihara, M. Takeda and Y. Arai, Chem. Pharm. Bull. 31 (1983) 1646.Google Scholar
  81. 81.
    K. Tsujihara, M. Ozeki, T. Morikawa, M. Kawamori, Y. Akaike and Y. Arai, J. Med. Chem. 25 (1982) 441.CrossRefGoogle Scholar
  82. 82.
    Y. Akaike, Y. Arai, H. Taguchi and H. Satoh, Gann 73 (1982) 480.Google Scholar
  83. 83.
    S. Fujimoto and M. Ogawa, Jpn. J. Cancer Res. (Gann) 76 (1985) 651.Google Scholar
  84. 84.
    B. Serrou, P.S. Schein and J.L. Imbach, eds, in Nitrosoureas in Cancer Treatment. Elsevier/North-Holland, Amsterdam (1981) p. 249.Google Scholar
  85. 85.
    S. Fujimoto and M. Ogawa, Cancer Chemother. Pharmacol. 9 (1982) 134.CrossRefGoogle Scholar
  86. 86.
    G. P. Wheeler, In Cancer Chemotherapy (ACS Symposium Series No. 3), ed. A.C. Sartorelli, American Chemical Society, Washington, DC (1976) p. 87.Google Scholar
  87. 87.
    T. P. Johnston, G. P. Wheeler, G. S. McCaleb, B. J. Bowdon and J. A. Montgomery, in Nitrosoureas in Cancer Treatment, eds. B. Serrou, P.S. Schein and J.-L. Imbach, Elsevier, New York (1981) p. 139.Google Scholar
  88. 88.
    E. R. Garrett, S. Goto and J. F. Stubbins. J. Pharm. Sci. 54 (1965) 119.CrossRefGoogle Scholar
  89. 89.
    W. J. Haggerty, Jr. and E. A. Murrell, Res./ Dev. 25 (1974) 30.Google Scholar
  90. 90.
    A. Meier, F. Stoos, D. Martin, G. Buyuk and E. Hardegger Helv. Chim. Acta 57 (1974) 2622.CrossRefGoogle Scholar
  91. 91.
    G. Eisenbrand, H. H. Fiebig and W.J. Zeller, Z. Krebsforsch Klin. Onkol. 86 (1976) 279.CrossRefGoogle Scholar
  92. 92.
    G. Kimura, U.S. Patent 4, 156,777 (1979).Google Scholar
  93. 93.
    T. P. Johnston, C. L. Kussner, R. L. Carter, J. L. Frye, N. R. Lomax, J. Plowman and V. L. Narayanan, J. Med. Chem. 27 (1984) 1422.CrossRefGoogle Scholar
  94. 94.
    J. Martinez, J. Oiry, J.-L Imbach and F. Winternitz, J. Med. Chem. 25 (1982) 178.CrossRefGoogle Scholar
  95. 95.
    J. Oiry, J. Martinez, J.-L. Imbach and F. Winternitz, Eur. J. Med. Chem, Ther. 16 (1981) 539.Google Scholar
  96. 96.
    H. E. May, R. Boose and D. J. Reed, Biochem. Biophys. Res. Commun. 57 (1974) 426.CrossRefGoogle Scholar
  97. 97.
    D. L. Hill, M. C. Kirk and R. F. Struck, Cancer Res. 35 (1975) 296.Google Scholar
  98. 98.
    J. Hilton and M. D. Walker, Biochem. Pharmacol. 24 (1975) 2153.CrossRefGoogle Scholar
  99. 99.
    D. J. Reed, in Nitrosoureas: Current Status and New Developments, eds. A.W. Prestayko, S.T. Crooke, L.H. Baker, S.K. Carter and P.S. Schein, Academic Press. New York (1981) p. 51.Google Scholar
  100. 100.
    J. Hilton and M. D. Walker, Proc. Am. Assoc. Cancer Res. 16 (1975) 103.Google Scholar
  101. 101.
    G. P. Wheeler, T. P. Johnston, B. J. Bowdon, G. S. McCaleb, D. L. Hill and J. A. Montgomery, Biochem. Pharmacol. 26 (1977) 2331.CrossRefGoogle Scholar
  102. 102.
    T. P. Johnston, G. S. McCaleb and J. A. Montgomery, J. Med. Chem. 18 (1975) 634.CrossRefGoogle Scholar
  103. 103.
    J. A. Montgomery, T. P. Johnston, H. J. Thomas, J. R. Piper and C. Temple, Jr. in Advances in Chromatogrpahy, Vol. 15, eds. J.C. Giddings, E. Gweshka, J. Cazes and P.R. Brown, Marcel Dekker, New York and Boston (1977) p. 169.Google Scholar
  104. 104.
    C. Hansch, N. Smith, R. Engle and H. Wood, Cancer Chemother. Rep. (Part I) 56 (1972) 443.Google Scholar
  105. 105.
    P. B. Farmer, A. B. Foster, M. Jarman, M. R. Oddy and D. J. Reed, J. Med. Chem. 21 (1978) 514.CrossRefGoogle Scholar
  106. 106.
    A. B. Foster, M. Jarman, P. L. Coe, J. Sleigh and J. C. Tatlow, J. Med. Chem. 23 (1980) 1226.CrossRefGoogle Scholar
  107. 107.
    R. J. Weinkam, T.-Y. J. Liu and H.-S. Lin, Chem.-Biol. Interact. 31 (1980) 167.CrossRefGoogle Scholar
  108. 108.
    J. A. Montgomery, Cancer Treat. Rep. 60 (1976) 651.Google Scholar
  109. 109.
    T. Anderson, M. G. McMenamin and P. S. Schein, Cancer Res. 35 (1975) 761.Google Scholar
  110. 110.
    J. M. Heal, P. Fox and P. S. Schein, Biochem. Pharmacol. 28 (1979) 1301.CrossRefGoogle Scholar
  111. 111.
    T. Machinami, S. Nishiyama, K. Kikuchi and T. Suami, Bull. Chem. Soc. Japan 48 (1975) 3763.CrossRefGoogle Scholar
  112. 112.
    T. Suami, K. Tadano and W. T. Bradner, J. Med. Chem. 22 (1979) 314.CrossRefGoogle Scholar
  113. 113.
    F. Shimuzu and M. Arakawa, Gann 66 (1975) 149.Google Scholar
  114. 114.
    R. Osieka, P. Glatte, R. Pannenbacker and C. G. Schmidt, Cancer Chemother. Pharmacol. 11 (1983) 147.CrossRefGoogle Scholar
  115. 115.
    D. Green, K. D. Tew, T. Hisamatsu and P. S. Schein, Biochem. Pharmacol. 31 (1982) 1671.CrossRefGoogle Scholar
  116. 116.
    D. Green, J. D. Ahlgren, and P. S. Schein, Nitrosoureas in Cancer Treatment, eds. B. Serrou, P.S. Schein and J.-L. Imbach, Elsevier North-Holland, Amsterdam (1981) p. 45.Google Scholar
  117. 117.
    T. P. Johnston, G. S. McCaleb, T. Anderson and D. S. Murinson, J. Med. Chem. 22 (1979) 597.CrossRefGoogle Scholar
  118. 118.
    M. Ogawa, in Nitrosoureas in Cancer Treatment, eds. B. Serrou, P. S. Schein and J.-L. Imbach. Elsevier North-Holland, Amsterdam (1981) p. 249.Google Scholar
  119. 119.
    H. Hasegawa and W. R. Shapiro, Proc. Am. Assoc. Cancer Res., ASCO 19 (1978) 153.Google Scholar
  120. 120.
    J.-L. Montero and J.-L. Imbach, C.R. Acad. Sci. Ser. C 279 (1974) 809.Google Scholar
  121. 121.
    J.-L. Imbach, J. Martinez, J. Oiry, C. Bournt, E. Chenn, R. Maral and C. Mathe, Nitrosoureas in Cancer Treatment eds. B. Serrou, P.S. Schein and J.-L. Imbach, Elsevier North-Holland, Amsterdam (1981) p. 123.Google Scholar
  122. 122.
    J. L. Rebischung, M. D. Gougeon, K. J. Mori, G. Lemaigre, G. Mathe and C. Jasmin, Cancer Res. 44 (1984) 503.Google Scholar
  123. 123.
    J.-L. Imbach, J.-L. Montero, A. Moruzzi, B. Serrou, E. Chenn, M. Hayat and G. Mathe, Biomedicine 23 (1975) 410.Google Scholar
  124. 124.
    G. Eisenbrand, M. Habs, W. J. Zeller, H. Fiebig, M. Berger, O. Zelesny and D. Schmahl, Nitrosoureas in Cancer Treatment, eds. B. Serrou, P.S. Schein and J.-L. Imbach, Elsevier North-Holland, Amsterdam (1981) p. 175.Google Scholar
  125. 125.
    F. Spreafico, S. Fillippeschi, P. Falantano, G. Eisenbrand, H. H. Fiebig, M. Habs, V. Zeller, M. Berger, D. Schmahl, L. M. VanPutten, T. Smink, E. Csqnyi and S. Somfai-Relle, in Nitrosoureas: Current Status and New Development, eds. A.W. Prestayko, L.H. Baker, S.T. Crooke, S.K. Carter and P.S. Schein, Academic Press, New York (1981) p. 27.Google Scholar
  126. 126.
    M. Miyahara, M. Nakadate, M. Miyahara, I. Suzuki, M. Ishidate, Jr. and S. Odashima,Gann 68 (1977) 573.Google Scholar
  127. 127.
    I. Baracu, G. Botez, R. Denes, V. Dobre, B. Ureche, T. Craescu, N. Voiculet and I. Niculescu-Duvaz, Rev. Roum. Biochim. 18 (1981) 175.Google Scholar
  128. 128.
    J. W. Lown, A. V. Joshua and L. W. McLaughlin, J. Med. Chem. 23 (1980) 798.CrossRefGoogle Scholar
  129. 129.
    J. L. Imbach, Personal communication.Google Scholar
  130. 130.
    T. P. Johnston and G. S. McCaleb, Unpublished results.Google Scholar
  131. 131.
    W. J. Zeller, M. Berger, G. Eisenbrand, W. Tang and D. Schmahl, Arzrneim-Forsch/Drug Res. 32 (1982) 484.Google Scholar
  132. 132.
    J.-L. Montero, A. Leydet, G. Dewynter, A. Seguin, J.-M. Favre and J.-L. Imbach, Eur. J. Med. Chem. Chim. Ther. 17 (1982) 257.Google Scholar
  133. 133.
    T. Suami, T. Kato, and T. Hisamatsu, in Nitrosoureas in Cancer Treatment, eds. B. Serrou, P.S. Schein and J.-L. Imbach, Elsevier North-Holland, Amsterdam (1981) p. 97.Google Scholar
  134. 134.
    T.-S. Lin, P. H. Fischer, G. T. Shiau and W. H. Prusoff, J. Med. Chem. 21, (1978) 130.CrossRefGoogle Scholar
  135. 135.
    P. H. Fischer, T.-S. Lin, M. S. Chen and W. H. Prusoff, Biochem. Pharmacol. 28 (1979) 2973.CrossRefGoogle Scholar
  136. 136.
    T.-S. Lin, P. H. Fischer, J. C. Marsh and W. H. Prusoff, Cancer Res. 42 (1982) 1624.Google Scholar
  137. 137.
    R. D. Elliott, R. W. Brockman and J. A. Montgomery, J. Med. Chem. 24 (1981) 350.CrossRefGoogle Scholar
  138. 138.
    R. D. Elliott, H. J. Thomas, S. C. Shaddix, D. J. Adamson, R. W. Brockman, J. M. Riordan and J. A. Montgomery, J. Med. Chem. 31 (1988) 250.CrossRefGoogle Scholar
  139. 139.
    J. A. Montgomery and H. J. Thomas, J. Med. Chem. 22 (1979) 1109.CrossRefGoogle Scholar
  140. 140.
    J. A. Montgomery, H. J. Thomas, R. W. Brockman and G. P. Wheeler, J. Med. Chem. 24 (1981) 184.CrossRefGoogle Scholar
  141. 141.
    J. R. Piper, G. S. McCaleb. J. A. Montgomery, F. A. Schmid and F. M. Sirotnak, J. Med. Chem. 28 (1985) 1016.CrossRefGoogle Scholar
  142. 142.
    A. M. Crider, C. K. L. Lu, H. G. Floss, J. M. Cassady and J. A. Clemens, J. Med. Chem. 22 (1979) 32.CrossRefGoogle Scholar
  143. 143.
    H.-Y. P. Lam, A. Begleiter, G. J. Goldenberg and C.-M. Wong, J. Med. Chem. 22 (1979) 200.CrossRefGoogle Scholar
  144. 144.
    F. I. Carroll, A. Philip, J. T. Blackwell, D. J. Taylor and M. E. Wall, J. Med. Chem. 15 (1972) 1158.CrossRefGoogle Scholar
  145. 145.
    A. M. Crider, T. M. Kolczynski and K. M. Yates, J. Med. Chem. 23 (1980) 324.CrossRefGoogle Scholar
  146. 146.
    G. Sosnovsky and S. W. Li, Life Sci. 36 (1985) 1479.CrossRefGoogle Scholar
  147. 147.
    P. Workman, Cancer Treat. Rep. 70 (1986) 1139.Google Scholar
  148. 148.
    R. T. Mulcahy, A. Carminati, J.-L. Barascut and J.-L. Imbach, Cancer Res. 48 (1988) 798.Google Scholar
  149. 149.
    A. Carminati, J.-L. Barascut, E. Chenut, C. Bourut, G. Mathe and J.-L. Imbach, Anticancer Drug Design 3 (1988) 57.Google Scholar

Copyright information

© Blackie & Son Ltd 1990

Authors and Affiliations

  • J. A. Montgomery
  • T. P. Johnston

There are no affiliations available

Personalised recommendations